Hydrazine hydrate (1:1) → 3H-Pyrazol-3-one, 4-(1,1-dimethylethyl)-5-(hydroxymethyl)-

HRID 276761Notes

Reaction equation

HRID 276761 reaction equation
[C:1]([CH:5]1[C:9](O)=[CH:8][O:7][C:6]1=[O:11])([CH3:4])([CH3:3])[CH3:2].O.[NH2:13][NH2:14]>CCO>[C:1]([C:5]1[C:6](=[O:11])[N:13]=[N:14][C:9]=1[CH2:8][OH:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18406868HCID 18406868, compound

Product 1

HCID 184068973H-Pyrazol-3-one, 4-(1,1-dimethylethyl)-5-(hydroxymethyl)-Yield 101.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-tert-Butyl-4-hydroxy-2-furanone (6.6 g, 42 mmol) was dissolved in EtOH (75 mL) with hydrazine hydrate (6.6 mL, 0.21 mol) and was heated at reflux for 16h. The solvent was evaporated and the residue azeotroped with xylene ( 3×50 mL) to afford the title compound (7.2 g, 100%) as a colourless solid. mp 169-172° C. 1H NMR (360 MHz, d6-DMSO) δ1.26 (9H, s), 4.41 (2H, d, J=5.2 Hz), 4.97-5.01 (1H, m), 9.30 (1H, br s), 11.05 (1H, br s). MS (ES+) 171 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16h
  3. customThe solvent was evaporated
  4. customthe residue azeotroped with xylene ( 3×50 mL)

Sources & evidence

ORD record
ord-fbf2da12e00044a4ad889c32a84ebbd7
Source dataset
uspto-grants-2002_03
Patent number
US06355638B1

Reaction notes

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